Hydrochloric Acid → 6-ethyl-N,N-dimethyl-2-methoxy-benzamide

HRID 22178노트

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HRID 22178 반응식
[CH3:1][N:2]([CH3:13])[C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH3:11].CN(C)[CH2:16][CH2:17]N(C)C.C([Li])(CC)C.C(Br)C.Cl>C1CCCCC1.CCC(C)C.O.O1CCCC1>[CH2:16]([C:9]1[C:4]([C:3]([N:2]([CH3:1])[CH3:13])=[O:12])=[C:5]([O:10][CH3:11])[CH:6]=[CH:7][CH:8]=1)[CH3:17]

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 6332Ethyl BromideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 111596462-Methoxy-N,N-dimethylbenzamideHCID 178418400CID 53628100

생성물 1

HCID 199273926-ethyl-N,N-dimethyl-2-methoxy-benzamide

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 19019564Cyclohexane isopentane용매

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온도
-70 °C

실험 절차

39.5 g of N,N-dimethyl-2-methoxy-benzamide and 28.5 ml of tetramethylethylenediamine are introduced into 190 ml of absolute tetrahydrofuran and the mixture is lithiated at -70° C. with 150 ml of a 1.4-molar sec-butyllithium solution in cyclohexane/isopentane. After subsequently stirring at -70° C. for 45 minutes, 25.6 ml of ethyl bromide are added dropwise within 25 minutes and the reaction mixture is then allowed to warm slowly to room temperature. Water is then added and the mixture is adjusted to pH 2 with hydrochloric acid and extracted twice with diethyl ether. The residue is purified on silica gel using ethyl acetate/n-hexane (4:6) to yield 6-ethyl-N,N-dimethyl-2-methoxy-benzamide in the form of a colourless oil, 1H-NMR (CDCl3): 3.82 ppm (m), 3.40 ppm (m) and 3.12 ppm (2q, N(CH2CH3)2), 2.56 ppm (m, CH2CH3).

후처리

  1. temperatureto warm slowly to room temperature
  2. extractionextracted twice with diethyl ether
  3. customThe residue is purified on silica gel

출처 및 근거

ORD 기록
ord-e236a500874a40a585bf4dcbacb3eccc
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428002

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